


'Would You Rather' and other ways to Annoy your Wizard

by thatoldeblackmagic



Category: Critical Role (Web Series)
Genre: Fluff, Gen, M/M, Pre-Relationship, annoying little sister Jester, sleepover games, who Caleb loves anyway
Language: English
Status: Completed
Published: 2018-06-15
Updated: 2018-06-15
Packaged: 2019-05-23 12:52:15
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,831
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14934605
Author URL: https://archiveofourown.org/users/thatoldeblackmagic/pseuds/thatoldeblackmagic
Summary: “Caleb.”  Jester slouches so far off the bed to the point where she is nearly on the ground.  “Caleb. Caaaleeeb, I’m bored.”  She reaches up and jabs her pointer finger into his cheek, twisting it so he can just feel a crescent dig into the side of his face.He’s been reading the same paragraph for a full minute now, none of the words even processing as distracted as he is, and Caleb knows well enough when a task is fruitless.  So, with a sigh, he shuts the book, brings it down semi-lightly onto Jester’s stomach, and says, “Hello bored.  I am Caleb.”





	'Would You Rather' and other ways to Annoy your Wizard

“Caleb,” Says the blue one as she annoys him on purpose. Jester is sprawled halfway across his and Nott’s shared bed, with her head almost off the edge and the rest of her spread over Caleb’s legs. The remainder of their crew are off on various errands, and Caleb is reading, or at least he’s trying to read since apparently Jester has made a game of pushing every single one of his buttons. He had even sequestered himself in his room, hoping that the closed door was enough of a demand for privacy to deter any obnoxious tieflings. He really should have known better. 

Frumpkin had kept her entertained for a little bit. It’s a good thing the cat is so tolerant and well behaved since Jester had decided to hoist Frumpkin up by his kitty armpits and perform a reenactment all of Beau’s “greatest hits”. It lasted for about 5 minutes before Frumpkin wisely abandoned them both and poofed back into his own dimension, leaving Jester with no one to bother but Caleb.

“Caleb.” Jester slouches so far off the bed to the point where she is nearly on the ground. “Caleb. Caaaleeeb, I’m bored.” She reaches up and jabs her pointer finger into his cheek, twisting it so he can just feel a crescent dig into the side of his face.

He’s been reading the same paragraph for a full minute now, none of the words even processing as distracted as he is, and Caleb knows well enough when a task is fruitless. So, with a sigh, he shuts the book, brings it down semi-lightly onto Jester’s stomach, and says, “Hello bored. I am Caleb.”

Jester perks up immediately. “Really?!” She all but shrieks as she scrambles back up into a sitting position. “That was such a bad joke which is saying a lot because all of your jokes are really bad. Not even Molly would have laughed at that one, and Molly laughs at all of your dumb jokes.”

“Did you come here just to insult me?” Caleb says, bringing the book down a little harder this time.

Jester just laughs and shifts herself over to rest against the back wall, throwing her legs into Caleb’s lap. “No, no, no. I came here to talk to you because we are friends and I am bored, and now that you are talking to me back I want to play a game!” She says in one long rush of breath, the words seemingly tumbling out one after the other. Jester straightens up, and reaches out to pat Caleb’s shoulder as if she doesn’t already have his attention. “So! Who do you think has the better butt, Fjord or Molly?”

Caleb opens his book and starts reading.

“No!” One of Jester’s legs rises up and drops back down to pin the book down against Caleb’s lap. “You can’t do that, you have to play the game!” She pats Caleb’s shoulder a bit harder in time with her syllables. “Who has the better tushy!! Tell me Caleb!” 

She is much stronger than him, and Caleb isn’t sure if he could escape even if he wanted to, though he finds that he is not uncomfortable with the physical contact. Actually, it's quite a testament to how far Caleb has progressed since they began this journey when he didn’t immediately try to push her off. Jester is still patting his shoulder, more punching than patting now, and if Caleb wants to avoid bruising he supposes he’ll have to play along. So Caleb sighs, now resigned to his fate, and replies. “I have to say Mollymauk since Fjord’s ass is so flat you could use it as a table.” 

The punching pauses, then rapidly increases as Jester starts to bounce on the bed. “You are so right! Fjord’s butt looks like it got hit really hard with a frying pan and then just stayed that way forever.” Which is certainly a way of putting it. Jester keeps bouncing, but stops punching, which Caleb decides to count as a win. “Okay, okay next question. Which part of Molly is the cutest? His horns or his tail?” 

Well that’s suspicious as hell. He doesn’t know how to respond because he doesn’t know what this is; if Jester is still playing a game, or if she has moved on to some sort of agenda. Caleb is leaning toward the latter, it seems that way at least, though the purpose of said agenda is not clear to him. Admittedly, not much is clear to him when it comes to Jester. She seems to live by a set of rules, or whims, that no one else can predict, least of all Caleb. He still is unsure what she wants from this game, if she truly wants anything other than company, but the fact of the matter is Caleb still can’t move. His legs have started to go numb while pinned under her weight and with his book inaccessible, he really has no choice.

Caleb goes for the safest route then says, “I don’t know. I can’t say I have a preference.”

“Sooo, you like them both equally then! That’s good because Molly would get all pouty if you didn’t like his tail or something.” Jester nods to herself quickly, then continues before Caleb can get a word in edgewise. “Oh! How about this, would you rather have Molly braid your hair, or get in a drinking contest with Beau?”

And just like that, Caleb understands. He’s seen Jester do this with Beau before, needling her until she gives in and starts gushing about Yasha, teasing her until Beau is red in the face. The main difference is that Beau is usually willing to play along. She has made it no secret where her affections lie, its just, Caleb thought that he had kept his own affections close to the chest. 

He truly thought he was a closed book on the matter of Mollymauk, no swooning or stuttering or even treating him any differently that Caleb treats the rest of their group. Caleb had even managed to convince himself for a short while that his feelings for Mollymauk were that of friendship, a strange sort of friendship brought about by close quarters and casual contact, but just friendship. Needless to say that didn’t last very long.

How Jester found out is a mystery. She’s more perceptive than they tend to give her credit for, Caleb knows that through many trials and errors, but he honestly, truly thought he could keep this cat in the bag for longer. 

Caleb sighs, and responds, “I think you are the only one having fun with this game.” He reaches out and taps the leg that is covering his book. “Up, please. I want to keep reading.” 

She doesn’t move. “Okayy fine you don’t have to answer that one because it was way to easy.” Jester settles deeper into the bed, half of her weight now leaning on Caleb. “Why don’t you ask me a question now?”

“No,” Caleb says as he tries in vain to pull the book out from under Jester’s legs without ripping any pages. 

“Why’re you so grouchy all of a sudden you grumpy butt?” Jester says, leaning forward to move even more of herself into Caleb’s space. She’s frowning now, the pouty kind of frown that is honestly more cute than upset, the kind of frown that clearly shows she isn’t actually going to stop this shit any time soon. “You’ve been reading all day, Caleb! Talk! To! Me!”

Caleb sighs, and looks down at the now crinkled pages of his book. “As I have already said, this game is not fun for me. I do not follow Beau’s tendency of blatant oversharing and I am certainly not one to think that reading all day is too much.” He turns back to look her in the eye and taps on her leg again. “Up.”

Again, she stays put. Though her head is tilted to the side and for some reason she looks confused. “What do you mean about Beau? She always gets super shady whenever anyone brings up her dad or jail or stuff.”

“You know that I’m not talking about those things.” Caleb says, but in reality he doesn’t know for sure. Jester playing dumb and Jester actually not understanding look very similar. It’s something she no doubt picked up from the environment in which she grew up, and has learned to perfect the whole “cute but ignorant” act to make people drop their guard. Though why she wants Caleb to drop his guard in this moment is somewhat of a mystery. 

She’s looking at him now, brow furrowed and lips pursed to one side. “You are not talking about those things.” Jester says to herself in a half-whisper. Then she’s mumbling so quickly and incomprehensibly that Caleb can’t even pretend to follow what she’s saying. It doesn’t seem like she intends for him to, as she begins to gesture to herself, putting pieces together that only she seems to understand. And that is what sets Caleb on edge. He thought- well, he assumed that he and Jester had been on the same page throughout their conversation. The only other thing that he thought-assumed was-

“Yasha?” Jester cuts off his thoughts in the way of one discovering a revelation. “So Yasha is Molly, then Beau is… you?”

And somehow, even Caleb can follow that train of thought. “No” He says far, far too late. “No, nein. That is not-”

“Caleb!” Jester cuts him off once more. “Caleb you have to tell me right now, do you like-like Molly?”

Caleb starts to feel actually, legitimately nauseous. “No.” He manages because he can’t have fucked up this badly. There has to be some way to salvage this situation, even if it means lying through his teeth to one of the few people he feels comfortable with. 

Jester just stares. She’s just looking at him now, tracking his slight movements, reading his face, and she knows. He can see it before she even speaks that she knows.

“Caleb,” She says gently this time, cautiously. “You don’t actually have to tell me if you don’t want to.” Jester pauses, contemplates, then continues, “It’s just that, if you ever DO want to I will totally be here to listen to you, and support you, and talk about how Molly is really really into you also. But, I do not want to make you uncomfortable so just know that I will be be here for you always, and I love you, and I think you and Molly would be so so cute together.”

Now it’s Caleb’s turn to stare. Scheiße. What a fucking statement. There are at least seven things that will take Caleb fifty eight minutes minimum to unpack fully, but somehow all his frazzled brain can come up with is, “I am already uncomfortable.” Then a beat, “What do you mean Molly is into me.”

Jesters face lights up like the fireworks during the harvest festival. “Molly likes you so so so much its really cute to watch! He’s super obvious about it and always hovers around you and one time I caught him watching you sleep by the fire.”

“Jester.” Caleb nervously runs a hand through his hair, pulling at the knots in the middle and fidgeting with the splits at the ends. He inhales, steadying himself, then continues, “One bombshell at a time please, if you don’t mind. I don’t- I mean- He hovers?”

“Yeah. LIke big time hovers. It’s really very sweet because he can tell when you don’t want the attention so he hovers from afar, kind of like when you send Frumpkin over to sit with Yasha you know?” Jester says, kicking her legs just enough that it jostles the entire bed.

And yes, Caleb does know. He had never thought of it as hovering, but essentially that’s what it is. He sends Frumpkin to be with Yasha because anxiety is a familiar beast, and Caleb is far too aware that another person nearby is often the worst way to help. It’s a little too easy for Caleb to associate this with Molly; reading a book by the fire at some inn in some town with Molly across the table shuffling his tarot cards for hours on end, taking the midnight watch in some half-frozen grassland as Molly hums lightly under his breath next to him, turning from a beast in battle to find Molly with his hand outstretched rendering that creature blind with its own blood. Caleb had never recognized these action as anything special because he had not known any better. It’s a certain kind of vertigo that overcomes Caleb as he puts together the pieces and realizes that Jester is on to something.

“Yes,” Caleb says slowly as a familiar warmth that he never once asked for floods his veins. “He hovers. That still doesn’t mean-” Caleb cuts himself off this time, because saying the words aloud would mean acknowledging their truth. But then again, “Does it?”

Jester is fucking beaming, kicking her legs like she just can’t hold it in, and she grabs Caleb’s hands, lacing their fingers together and squeezing tight. “Yes it does Caleb! Believe me it does. Sometimes he just won’t shut up about it and your name does not translate very well to Infernal.”

It startles a laugh out of him, just a small one, as he unlaces a hand from Jesters and drags it hand across his face. “Scheiße.” Caleb presses the heel of his palm over the bridge of his nose and says, “I think I do too. Or well, I know I do. I’m familiar with how I feel, I just didn’t think I’d experience it again, at least not so soon; not this strong.” He drops his hand back to Jester’s and lets out a long sigh. “Jester, can you keep this between us?”

“Oh.” Jester says, and quickly relaces their hands together. “You’re not going to say anything to him.” She states with a soft understanding. Jester, as always, is more perceptive that Caleb thinks; thought perhaps more empathetic is the right term. 

“No.” Caleb shakes his head, turning back toward the book still pinned beneath Jester’s legs. “We have only known each other a short while, and I have no way of knowing where we all will be in a few month’s time. I do like Molly, I like him very much, but I want there to be certainty before action. Do you get what I mean?”

Jester shrugs. “Sort of? I get wanting to be certain, but I don’t know what knowing each other for longer has to do with that. But, either way I won’t tell your secret!” Jester holds out her right pinky, waving in front of Caleb. “I swear.”

Caleb looks Jester dead in the eye as he slowly lifts his right hand in the air with his pinky raised. “And who do you call upon to uphold this oath?”

Jester sits up, ramrod straight with a smile playing at her lips as she says, “I swear on the almighty and magnificent Pumat Sol, and Pumat Sol, and Pumat Sol, and-”

“May their glorious name live on forever.” Caleb interrupts, and links their pinkies together.

Jester dissolves into laughter and collapses on top of Caleb, pressing her horns a bit uncomfortably into his sternum. “I hope you will be certain enough to tell him someday soon.” She states once her laughter dies down. 

“I do too.” Caleb says with complete honesty. 

Jester is all but tucked into Caleb's side now, and is crushing his arm against the back wall. With some maneuvering and a maybe on purpose jab to Jester's side, Caleb is able to free his arm and let it come down to rest over Jester's shoulders. She's starts singing, a bouncy tune in a language that Caleb doesn't understand, as she finally shifts her legs off of Caleb's lap so she is able to further curl into his side. Caleb snatches his poor crumpled book before Jester decides to change her mind, and she laughs again, reaching out to smooth down some of the bent pages. "Can you read it out loud? Maybe we can switch off reading like they make you do in school!"

"Sure," Caleb responds because he's come to find that its a bit hard for him to deny Jester anything. Though its certainly not the worst thing, especially when Jester gives all of herself just as freely to Caleb whether he asks for it or not. 

So they read. Jester makes up voices for the different paragraphs even though there isn't much dialogue in this 500 page Ritual Spell book, and Caleb indulges her by doing the same. It's easy, it makes her laugh, and although Caleb isn't certain about all the relationships in his life, he's glad he can be certain about this one.

**Author's Note:**

> I love Caleb and Jester's sibling-like relationship and all i want is more annoying little sister Jester.
> 
> I'm planning a part 2 to this where Caleb gets his shit together and Jester wingmans so so good, but I wanted this to be a stand alone fic! Sorry for the distinct lack of Molly, but I promise he'll be around soon


End file.
